Potassium Cyanide → 3-(2-Chlorophenyl)-3-hydroxypropanenitrile

HRID 1913862Notes

Reaction equation

HRID 1913862 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:10][O:9]1.[C-:11]#[N:12].[K+].C(=O)([O-])O.[Na+]>C(O)C.O.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:9])[CH2:10][C:11]#[N:12]

Participants

7

Reactant 3

HCID 9032Potassium CyanideHCID 516892Sodium BicarbonateHCID 5607092-(2-Chlorophenyl)oxirane

Product 1

HCID 119754983-(2-Chlorophenyl)-3-hydroxypropanenitrileYield 64%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

2-(2-chloro-phenyl)-oxirane (440 mg, 2.85 mmol) was dissolved in ethanol (3 mL) and treated with potassium cyanide in water (3 mL) and hydrogen chloride (4 M in 1,4-dioxane, 0.71 mL) subsequently. The mixture was stirred at 50° C. for 8 hr and room temperature for overnight. Saturated sodium hydrogen carbonate was added and the mixture was concentrated. The residue was extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (40 g silica gel cartridge) eluting with ethyl acetate/hexane (0%-30%) to give the product as a colorless oil (330 mg, 64%). 1H NMR (CDCl3) δ 7.70-7.60 (m, 1H), 7.40-7.20 (m, 2H), 5.50-5.40 (m, 1H), 2.98-2.85 (m, 1H), 2.85-2.80 (m, 1H), 2.78-2.65 (m, 1H).

Workup

  1. concentrationthe mixture was concentrated
  2. extractionThe residue was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by column chromatography (40 g silica gel cartridge)
  5. washeluting with ethyl acetate/hexane (0%-30%)

Sources & evidence

ORD record
ord-95b541edcc4c4f498ee27486ae70f75a
Source dataset
uspto-grants-2013_12
Patent number
US08609849B1

Reaction notes

Loading…